hydrogen; palladium on activated charcoal in methanol P=2250.18 Torr; 14 h;

1: 85 percent / DIPEA; DMAP / CH2Cl2 / 5 h / 20 °C 2: 85 percent / NaN3; NH4Cl / methanol / 40 h / Heating 3: 72 percent / m-chloroperbenzoic acid / CH2Cl2 / 20 °C 4: 82 percent / Yb(OTf)3; Et3N; NaN3 / molecular sieves 4 Angstroem / toluene / 96 h / 80 °C 5: 100 percent / HCl / methanol / 20 °C 6: 95 percent / H2 / Pd/C / methanol / 14 h / 2250.18 Torr View Scheme

1: 100 percent / HCl / methanol / 20 °C 2: 95 percent / H2 / Pd/C / methanol / 14 h / 2250.18 Torr View Scheme

water; hydrogen bromide T=120°C; 17 h; Inert atmosphere;

1: H(+) / CH2Cl2 2: sodium borhydride / ethanol 3: 2.) H(+) / 1.) pyridine; 2.) MeOH 4: sodium azide / dimethylformamide View Scheme

ion exchanger (Amberlite IRA 410 OH(-))

hydrogenchloride

hydrogenchloride 1.5 h; Heating; Title compound not separated from byproducts;

hydrogenchloride 18 h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

hydrogenchloride; sodium tetrahydroborate; acetic anhydride in water incorporation of doubly labelled precursors; (6RS)-D-<6-14C,6-3H>glucose; Mechanism;